Water → HCID 131716772, compound

HRID 704732Notes

Reaction equation

HRID 704732 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[N:25]([CH2:26][C:27]3[N:28]=[CH:29][S:30][CH:31]=3)[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]=2)[CH2:12]1.[C:32](=[O:35])([O-])[O-:33].[Na+].[Na+].CN(C)C(=[O:42])C.[OH2:44]>>[C:32]([OH:33])(=[O:35])/[CH:4]=[CH:5]/[C:6]([OH:42])=[O:44].[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[NH:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[N:25]([CH2:26][C:27]3[N:28]=[CH:29][S:30][CH:31]=3)[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]=2)[CH2:12]1

Participants

6

Reactant 5

HCID 962WaterHCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 744042-ChloropyrimidineHCID 15037417HCID 15037417, compound

Product 1

HCID 131716772HCID 131716772, compoundYield 32.1%

Conditions

Temperature
100 °C

Procedure

A mixture of 1.7 parts of 2-chloropyrimidine, 4.1 parts of N-[1-(2-aminoethyl)-3-pyrrolidinyl]-3-(4-thiazolylmethyl)-3H-imidazo[4,5-b]-pyridin-2-amine, 2.1 parts of sodium carbonate and 108 parts of N,N-di-methylacetamide was stirred for 6 hours at 100° C. After cooling, the reaction mixture was poured into 600 parts of water and the product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in 2-propanone and ethanol. The salt was filtered off, washed with 2-propanone and crystallized from a mixture of 2,2'-oxybispropane and methanol (1:1 by volume). The product was filtered off, washed with 2-propanone and dried in vacuo at 60° C., yielding 3.0 parts (32.1%) of N-[1-[2-(2-pyrimidinylamino)ethyl]-3-pyrrolidinyl]-3-(4-thiazolylmethyl)-3H-imidazo[4,5-b]pyridin-2-amine (E)-2-butenedioate(1:3), hemihydrate; mp. 161.7° C. (compound 155).

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with dichloromethane
  3. washThe extract was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt was filtered off
  8. washwashed with 2-propanone
  9. customcrystallized from a mixture of 2,2'-oxybispropane and methanol (1:1 by volume)
  10. filtrationThe product was filtered off
  11. washwashed with 2-propanone
  12. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-ccae067b4a744da3b1363cce04d3b252
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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